Cakl kbatjhs



Patented Nov. 22, 19.27.

UNITED STATES,

cam. KRAUI-IS, on LEVERKUSEN, NEAR coLoenn, GERMANY, assrenon TOGRAssELLI nYEsTUFF oonrona'rron, on new YORK, N. x, A CORPORATEON orDELAWARE.

VAT DYES'IUFF on THE rserrnn oxx'rnionarnrnnnnenour.

No Drawing. Application filed January 5, 1926, Serial No. 79,472, and.in Germany January 8; 1925.

The unsubstituted isatine obtained from aniline when condensed withoxythionaphtheneyields a dyestulf which produces dyeings ofpronouncedredshades. Likewise, according to my determination,(i-methylisatine obtained frominetafoluidine and 5 methylisatineprepared from para-toluidine yield dyestuffs which produce pronouncedred dyeings which vary Very little from each other in shade.

. I have now found in contrast to these substances that "Z-methylisatineobtained from ortho-toluidine yields with oxythionaphthene a dyestuffwhich surprisingly, produces an entirely different shade, namely, a veryyellow-brown. In particular, it was unexpected that 5-1nethylisatine and7-methylisatine combined with oxythionaphthene' would produce colorsh'ades which differ from each other so completely.

This very surprising difference of shade manifests itself also in thefurther substituted 7 -methylisatines. The dyestuif from 6-chlor-5methylisatine and oxythionaphthene dyes a deep brownish Bordeaux; whileon the other hand, the corresponding dyestuii' from6-chlor-7-methylisatine dyes an orange-like Very yellow red.

, These vat dyestuffs obtained by the cou- "pling of 7-methylisatineswith oxythionaphthemes are when dry yellow-brown to brownred powders.They dissolve in concentrated sulfuric acid and yield blue to violetcolored solutions. The color of their vat solutions is yellow. I

The alpha-derivatives of 7-1nethylisatine also give a very surprisingresult when com bined with oxythionaphthene. lVhile 7-7- dimethylindigodyes a greener and duller color than does ordinary indigo, 7-methyl-2- Iindole-Z-thionaphtheneindigo yields redder and clearer shades than does2-indole-2-thionaphthcneindigo. thio'naphtheneindigo dyes a rich greyishand dull violet. On the other hand, T-methylindolethionaphtheneindigohalogenated in the same way yields violet colored dyeings of pronouncedclearness.

Halogenated 7 -inethylindolethionaphtheneindigo in the dry state is ablue-violet powder. Its solution in concentrated sulfuric acid isgreenish-blue and the color ofits vat Halogenated 2-indole-2 solution isyellow. It probably lown constitutional formula:

Hal.

PATENT OFFICE.

in which the position of the halogen atoms (Hat) is not perfectly known.

Example 1.

I "Na-o0" i s i=o r do 7 Example 2. I

6-chlor-7 -1netl1ylisatine obtained as in German Patent 277,396 grantedJuly 13, 1914 to I. G. Farbenindustrie Aktiengesellschaft is combinedwith oxythionaphthene in the manner described in Example 1. Thedyestufl' produced dyes textile fibres yellowred to orange shades. Thedyeings are out-' standingly fast. When'dried the dyestuff is abrown-red powder. Its solution in sulfuric acid is violet colored andthe color of itsvat solution is yellow. It probably has the followingconstitutional formula 01 l NH\ s 1 00 .L/alO Example 3..

7-methylisatine-alpha-ortho-toluidine preat about 60.

in Which the position of the bromine atom is not perfectly known.

A further example of the striking dif-.

ferences in color manifested by the methylisatines is the differencebetween 5 'T-diohlorisantine 6 chlor-7 methyloxythionaphthene and 6chlor-7-methylisatine-6-chlor-7-methyl0Xythio-naphthene. The formerproduces dark maroon-colored dyeings while the latter yields a verybrownish-orange dyeing.

It is evident that the dyestuffs made according to this invention may beregarded as condensation products of 7-methylisatine;

its derivatives substituted in the benzene nucleus; or their reactivealpha derivatives, and oxythionaphthene compounds;

obtained by linking oxythionaphthene compounds with either the alpha orbeta carbons of lsatine and the term condensatlon products of7-methylisatines and oXythio-v naphth-enes in the claims is intendedto'inelude all such condensation products which are derivatives of theT-methylisatines.

' I claim:

1. As new products, vat dyestuffs which are substantially identical withcondensation products of 'T-methylisatines and oxythionaphthenes.

2. As new products, vat dyestuifs which may be regarded as condensationproducts of halogenated 7-methylisatines and oxythionaphthenes.

3; As new products, vat dyestuffs which a s substantially identical withcondensation products of chlorinated and oxythionaphthenes.

4. A vat dyestufi' which is the condensation productof(v-chior-7-1nethylisatine and oizythionaphthene.

5. A vat dyestuif, which is substantially identical with thecondensation product of (S-chlor-?-inethylisatine and oxythionaphthene,which probably has the constitutional formula CH3 01 NH s t=o which inthe dry state is a brown-red pow- CARL KRAUHS.

T-methylisatines

